Acetic Acid → 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine

HRID 2194985ノート

反応式

HRID 2194985 の反応式
[CH:1]1([NH2:4])[CH2:3][CH2:2]1.C(O)(=O)C.[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[C:17](=O)[CH2:16][CH2:15]2.C([BH3-])#N.[Na+]>CO>[Cl:9][C:10]1[CH:11]=[CH:12][CH:13]=[C:14]2[C:18]=1[CH:17]([NH:4][CH:1]1[CH2:3][CH2:2]1)[CH2:16][CH2:15]2

参加物

6

反応物 4

HCID 176Acetic AcidHCID 69828CyclopropylamineHCID 5003444Sodium cyanoborohydrideHCID 112174497-CHLORO-1-INDANONE

生成物 1

HCID 684283077-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine収率 89.9%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a cooled solution of 4.16 ml (60 mmol) of cyclopropylamine and 4.3 ml (75 mmol) of acetic acid, together with 5 g of 3 Å molecular sieves, in 80 ml of methanol, are added 5 g (30 mmol) of 7-chloro-2,3-dihydro-1H-inden-1-one. The reaction mixture is stirred for 4 hrs at reflux. The reaction mixture is then cooled to ambient temperature and 2.83 g (45 mmol) of sodium cyanoborohydride are slowly added. The reaction mixture is further stirred for 2 hrs at reflux. The solvent is removed under vacuum and 100 ml of water are then added to the residue and the pH is adjusted to 10 with sodium hydroxyde. The watery layer is extracted three times with dichloromethane (3×50 ml); the combined organic layers are dried over magnesium sulphate and concentrated in vacuum to yield 5.6 g (80% yield) of 7-chloro-N-cyclopropyl-2,3-dihydro-1H-inden-1-amine as an brown oil (M+1=208).

後処理

  1. temperatureat reflux
  2. stirringThe reaction mixture is further stirred for 2 hrs
  3. temperatureat reflux
  4. customThe solvent is removed under vacuum and 100 ml of water
  5. additionare then added to the residue
  6. extractionThe watery layer is extracted three times with dichloromethane (3×50 ml)
  7. dry with materialthe combined organic layers are dried over magnesium sulphate
  8. concentrationconcentrated in vacuum

出典と根拠

ORDレコード
ord-9758f4da96df4d5ca1e3b8b40fb6a742
出典データセット
uspto-grants-2012_12
特許番号
US08334390B2

反応ノート

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